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Portraits: The First Ladies of Menswear

Our favourite women in menswear 

I dress for myself. Not for the image, not for the public, not for the fashion, not for men. — Marlene Dietrich

Getting dressed is about a lot more than covering your body; your clothes can speak to who you are as a person in ways you don’t need to vocalise.

Here are some of our favourite women who choose to make a statement in items traditionally reserved for men.

I dress for myself. Not for the image, not for the public, not for the fashion, not for men. — Marlene Dietrich

Catherine Deneuve

The actress with designer Yves Saint Laurent in a Helmut Newton photo shoot in 1981 to mark the 20th anniversary of YSL. The designer revolutionised fashion by bringing a menswear aesthetic to womenswear, including with the “Le Smoking” suit — a tux women could wear to formal affairs.

Grace Jones

The supermodel, singer, songwriter, record producer and actress was a star of Studio 54 and has worked with the biggest names in entertainment. Her biggest role was as May Day in the 1985 James Bond movie A View to a Kill, although she did most of her own stunts in 1984’s Conan the Destroyer. Andy Warhol, Keith Haring, Robert Mapplethorpe and Jean-Paul Goude were high-profile collaborators. Jones is known for her distinctive style and bold features, and was a muse for the likes of Issey Miyake and Thierry Mugler.

Casey Legler

The former Olympic swimmer became the first woman signed to modelling agency Ford’s men’s division, in 2012. A favourite of photographer duo Inez and Vinoodh, she’s appeared in campaigns for the likes of AllSaints and Diesel and has done a 30-page editorial with Peter Lindbergh. These days the 6ft 2in writer and restaurateur chooses to focus on her art, but her commitment to non-conformity has blazed a trail for non-binary catwalk stars such as Teddy Quinlivan and Oslo Grace.

Lady Gaga

The pop star known for her statement outfits stunned at the Elle Women in Hollywood celebration in this oversize Marc Jacobs suit, reportedly after trying on more than 10 dresses. In a tearful talk she discussed being sexually assaulted at age 19 by “someone in the entertainment industry”, and called for mental health issues to be prioritised. “Today, I wear the pants,” she said. “I had a revelation that I had to be empowered to be myself today more than ever, to resist the standards of Hollywood, whatever that means. To resist the standards of dressing to impress and to use what really matters — my voice.”

Katharine Hepburn

Hollywood wasn’t ready for Hepburn when she burst onto the screen in the early-1930s — she boldly wore trousers at a time when women could be imprisoned for doing so. Alongside contemporaries Greta Garbo and Marlene Dietrich, the American actress challenged clothing norms on screen and off. Her audacious style has led to enduring status as a fashion icon.

Janelle Monáe

She adopted the alter ego Cindi Mayweather, a time-travelling android, early in her career as a “protective armour”, she told Rolling Stone of the black-and-white androgynous look that’s been her signature. “It had to do with the fear of being judged.” These days the woman behind one of the best albums of 2018 — Dirty Computer — incorporates colour, but the essence is still there. She still serves expressive and avant-garde looks that are uniform-like at the same time.

Marlene Dietrich

“I dress for myself. Not for the image, not for the public, not for the fashion, not for men.” The German actress was the epitome of style and sophistication, and oozed sensuality and glamour — and she did so on her own terms. She was equally striking in a sequined gown and fur coat as she was in a suit and fedora, a feat few can achieve.

Kristen Stewart

The Twilight actress first rebelled against the Cannes’ festival’s controversial red carpet flats ban back in 2016, and made headlines again this year for ditching her Christan Louboutin stilettos on the carpet for the BlacKkKlansman screening. This look, to the premiere of Knife + Heart, makes a different statement — one that explains her status as a menswear icon: A white button-up worn as a crop top, open at the bottom, paired with a long black blazer, black trousers, black loafers and a slicked-back hairdo.

“My style says ‘Look at me, don’t look at me.’ It’s, ‘I don’t care what you think.’”

Patti Smith

The Godmother of Punk was also the Queen of Understated Cool. The author-artist-musician cultivated a menswear-inspired look long before it became fashionable, rocking collared shirts and loose neckties under blazers with trousers or jeans and boots. Pictured here at the Roundhouse in London in 1975, her easy style is as relevant today. In an interview with the New York Times, she described it as: “My style says ‘Look at me, don’t look at me.’ It’s, ‘I don’t care what you think.’”

Annie Lennox

The Scottish musician, activist and philanthropist became known globally for the men’s suits she wore as Eurythmics frontwoman in the ’80s. Bright suits, bold prints, oversized trench coats — she wore them all, and even threw in hats and military-style accents. Lennox’s sartorial sense is so iconic that it inspired a collection by Dolce & Gabbana in 2011. On her style, she told Interview magazine: “It was how I felt and wanted to portray myself. I played with the image, because I think image is temporary. It’s a projection. It’s illusory.”

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